Five must-see Italian hill towns in Tuscany and Umbria

A view of the Tuscan countryside near Cortona.

With a sweep of his hand, Sergio Dondoli expounds on the makings of his famous gelato, winner of the World’s Best award more than once and the main offering of his shop off the main square in the medieval hill town of San Gimignano in Tuscany, Italy.

As guide Belinda Richardson translates for a group of visiting travel writers, across the piazza owners of a rival shop can be seen tisk-tisking Sergio’s performance as they stand in front of their own sign claiming to have the “world’s best ice cream.”

In centuries past, they might have stormed over and knocked down Sergio’s tower.

San Gimignano, also known as the medieval Manhattan, is noted for its towers, once the pride of feuding families. Anyone who read Romeo and Juliet for high school English knows of the feuding Montagues and Capulets in long-ago Florence, but a history of conflict also runs under the scorching Tuscan sun, amid the wineries, olive groves and Cyprus pines that provide a postcard backdrop, and is at the heart of a series of hill towns dotting Umbria and Tuscany between Rome and Venice, centred by the university town of Perugia.

“San Gimignano is quintessentially Medieval, known as the Medieval Manhattan,” explains Richardson, who lives in a centuries-old farm house and grows olives in the region and leads groups for Insight Vacations.

“In its heyday, it was bristling with over 72 tall towers. During the 12th to 14th centuries the towers grew storey upon storey as bitter rivalries escalated between competing saffron merchants, like the Guelphs and the Ghibellines.

“Think Shakespeare’s Montagues, who supported the Holy Roman Emperor and Capulets who supported the Pope. Like a civil war, each warring family battled out their quarrels in these tower houses. Living at the bottom, they used the top of the tower to fire arrows, catapults, stones, boiling oil when needed. If they lost, they lost their tower, whose height reflected their power and wealth. These towers were about 70 metres and must have been a sight to the pilgrims who used this town as one of their transit stops en route to Rome.”

Ultimately the feuding in San Gimignano was for naught as the town’s population was decimated by the black plague that didn’t take sides. Today, it stands as an near perfectly preserved UNESCO world Heritage site, its remaining towers stretching up into the blue sky during my visit to Italy’s most famed rural region.

Here are five more must-see towns in Umbria and Tuscany:

Orvieto: Back in Umbria, Orvieto was the major centre of the Etruscan people who travelled to the region with the Greeks by boat, constructed on the top of a steep hill of a volcanic ash stone called tufa, Amid the winding streets, and trunks of towers cut down by enemies, it is also home to chef Lorenzo Polgeri, The Etruscan Chef, who offers hearty fare and cooking lessons out of his restaurant (called Zeppelin after the band) and soon in a new establishment he and partner Kim Brookmire are building nearby. “Umbria is the green mystical heart of Italy,” says Polgeri. “It’s Tuscany’s little sister: less discovered.”

At the town’s highest point is a candy-striped cathedral most notable for the relief images carved out of marble showing Dante’s versions of hell.

Perugia: Marked by a crossing of the River Tiber, Perusia is Umbria’s capital, located north of Rome and southeast of Florence. It covers a high hilltop and part of the valleys around the area. Perugia was one of the main Etruscan cities that today is a hilly university town in the news recently for the sensational Amanda Knox murder trial. An important centre for medieval art, escalators take visitors up through the remains of a 16th-century fortress built on top of medieval streets and covered with brick ceilings.

Assisi: Here the Tufa buildings of Orvieto have given way to sandstone.

The home of St. Francis, Assisi draws more than five million visitors a year, so many of them from Poland that many interpretive signs are in Italian, English and Polish.

“It is one of the places where art, history and religion merge,” says Marco Ballanca, a local historian and guide who also worked with police in the early stages of the Knox case in Perugia. “St. Francis saved the (Catholic) church by bringing it back to the people.”

Francis himself is entombed in Papal Basilica of St. Francis of Assisi as is his spiritual assistant St. Clare, a noblewoman who founded an order of nuns now called the Poor Clares.

Spello: If it weren’t for the beautifully decorated doorways, bursting with potted flowers, it would be easy to think of the village of Spello as deserted. Again, the winding narrow streets and two-storey stone buildings dominate, but the town also features one of the best-preserved Roman walls in Italy and is famed for its annual flower festival, when residents stay up all night creating beautiful flower carpets for vesting bishops to walk on.

“It’s a year of work, but they do it because they love this place so much,” says Ballanca.

Cortona: Highlighted beautifully by the writing of Frances Mayes, Cortona is perhaps the best known of these towns under the Tuscan sun. Past the church at the top of a hill is the main piazza, with a stunning view of the countryside off the back. It’s that geography, combined with the preserved history of the town, that has drawn writers and artists to the area for ages.

Back in San Gimignano, after finishing a bowl of Sergio’s gelato, I wander back to the main street leading down from the piazza, but hang a left on a street winding behind the buildings that line the square. There I’m confronted with the dazzling views of the Tuscan countryside. It’s the reverse of a view we’d stopped for earlier that morning of vineyards and Cypress pines rising up to the village in the distance.

It’s those images and immersion in layers of rich history that draw visitors from the world over and help make Italy the No. 1 destination for Alberta travellers.

Family at heart of Italian food and wine

One is a count with the aristocratic good looks that make women swoon, the other a simple farmer with an uncanny resemblance to Bruce Springsteen. Both exemplify the family-based core of Italy’s food culture.

While “eat local” has become a buzz word for foodies, in Umbria and Tuscany it is a way of life that spans centuries.

Take Francesco Mazzei for example. He’s the 26th generation of his family to run the Mazzei family winery in a tiny village of Fontuertoli in the Chianti region of Tuscany.

“We have been here for six centuries,” says Francesco during a tasting of the winery’s offerings. “We are very proud. The village is a little jewel.

We are up in the hills where it is very rocky and very little soil. So, we are very low yield. Each vine produces not even a bottle so we have to stay very low yield. But we get some great wines.”

Recently, Mazzei has expanded somewhat to include an automated bottling facility and now exports wines to 25 countries. In total, the winery includes 650 hectares of specialized varieties between 250 and 500 metres above sea level. The focus of most of the winery’s production is the Sangiovese grape.

Francesco, who after university worked for a number of corporations before returning to the family business in 1996, says the biggest change he’s seen in the wine business is the shift in how wine is consumed. Once just a drink to wash down dinner, it is now a treat and treated as gourmet fare.

“Wine was once just part of the (diet). Now it is for pleasure.”

On top of producing wine the Mazzei estatealso hosts visitors in 12 country-themed rooms with spectacular views of the surrounding hills and valleys.

As for the next generation, Francesco says the winery will remain in the family, but under whom is to be determined.

“We have a bunch of people to choose from,” he says. “There are three boys and eight girls in the next generation. So, we will see.”

If wine is at the upper end of Italian cuisine, olives are at its base, and the family-owned Farm Ragani in Umbria has for generations produced extra virgin olive oil through the cold pressed methods passed down through generations.

As soon as they’re picked from groves at 350 metres above sea level on the slopes of Mount Subasio in the hills of Assisi and Spello, the olives are trucked to the farm’s small olive mill. There, explains Manuela Ragani, they are crushed by two large granite wheels. The resulting paste is spread on plates that are then stacked and pressed to produce a greenish oil, the sooner enjoyed the better.

Again, rocky soil adds flavour to the oil, giving it a strong, bitter and spicy flavours. “They’re so genuine. So Italy,” says local guide Belinda Richardson. “(Witnessing the production of olive oil) You see how people love the place.”

If You Go

Insight Vacations offers tours around the world using spacious coaches with every second seat removed for more leg room, and industry-leading guides giving insider information on all of Italy’s top sights. Insightvacations.com, 1-866-747-8120. These are not you parents’ bus tours of old.

WestJet and AirCanada with partners offer flights from Calgary to Rome.

We encourage all readers to share their views on our articles and blog posts. We are committed to maintaining a lively but civil forum for discussion, so we ask you to avoid personal attacks, and please keep your comments relevant and respectful. If you encounter a comment that is abusive, click the "X" in the upper right corner of the comment box to report spam or abuse. We are using Facebook commenting. Visit our FAQ page for more information.

Almost Done!

Postmedia wants to improve your reading experience as well as share the best deals and promotions from our advertisers with you. The information below will be used to optimize the content and make ads across the network more relevant to you. You can always change the information you share with us by editing your profile.

By clicking "Create Account", I hearby grant permission to Postmedia to use my account information to create my account.

I also accept and agree to be bound by Postmedia's Terms and Conditions with respect to my use of the Site and I have read and understand Postmedia's Privacy Statement. I consent to the collection, use, maintenance, and disclosure of my information in accordance with the Postmedia's Privacy Policy.

Postmedia wants to improve your reading experience as well as share the best deals and promotions from our advertisers with you. The information below will be used to optimize the content and make ads across the network more relevant to you. You can always change the information you share with us by editing your profile.

By clicking "Create Account", I hearby grant permission to Postmedia to use my account information to create my account.

I also accept and agree to be bound by Postmedia's Terms and Conditions with respect to my use of the Site and I have read and understand Postmedia's Privacy Statement. I consent to the collection, use, maintenance, and disclosure of my information in accordance with the Postmedia's Privacy Policy.